Rule interpretation in general
There are two points to remember when looking at an ambiguous rule:
Your group, with the DM as final arbiter, decides the ruling for the rule. So, you need to establish what this is for each group that you play with.
Specific beats general. Start with the most general rule you can find and see how the specific rules change this.
Armor resizing in particular
For your issue, start with PHB p. 145 (ignoring the optional part because it makes no difference to the case at hand)
Variant: Equipment Sizes
In most campaigns, you can use or wear any equipment that you find on your adventures, within the bounds of common sense. For example, a burly half-orc won't fit in a halfling’s leather armor, and a gnome would be swallowed up in a
cloud giant’s elegant robe.
There's your general rule: no armor that fits a PC race (size S or M) would fit a bear (size L).
Wild Shape (p. 67 PHB) says:
Worn equipment functions as normal, but the DM decides whether it is practical for the new form to wear a piece of equipment, based on the creature’s shape and size. Your equipment doesn’t change size or shape to match the new form.
No help there; the armor will be too small and the wrong shape. In addition, there is a ruling that has to be made right here: is it practical for a bear to use armor even if it is the right size and shape? My ruling would be yes but your results may differ.
Now from DMG, p. 140:
In most cases, a magic item that's meant to be worn can fit a creature regardless of its size or build. Many magic garments are made to be easily adjustable, or they magically adjust themselves to the wearer.
The ruling needed here is does the hide armor a) need easy adjustment or b) magically adjust itself. If b) then all is easy, if a) then the druid may need to allow it to drop to the floor and then get some assistance to put it on which would take 5 minutes (PHB, p. 146) which makes it pretty useless in combat.
Those are the issues; your group needs to make the ruling.
As others have stated, no you can not use a focus (of any kind) while Wild Shaped, even if the animal you morph into has hands, and they are empty and holding the focus. All of the information you posted in the original question provides the answers for you so long as you cross reference them. But a lot of people have missed a crucial part of why it can't be done.
The description of the Druidic Focus says (5e PHB, p. 151):
A druidic focus might be [...] a totem object incorporating feathers,
fur, bones, and teeth from sacred animals. A druid can use such an
object as a spellcasting focus.
This essentially states that you get to create a focus out of whatever you deem worthy to call a focus; pretty neat.
The description of Material (M) components says:
Casting some spells requires particular objects, specified in
parentheses in the component entry. A character can use [...] a
spellcasting focus in place of the components specified for a
spell [but not costly or consumed components]
This is the start of the unravel. Here it says you can use a focus instead of a material component (so long as it has no cost/isn't consumed). So essentially focuses are just fluff/filler for material components that most people over look anyway, but if you don't overlook that stuff it's still a pretty minimal net gain.
Part of the description of the druid's Wild Shape feature says (5e PHB, p. 67):
- You choose whether your equipment falls to the ground in your
space, merges into your new form, or is worn by it. [...]
This portion infers that you get to wear or hold your focus if you so choose when you Wild Shape, which is pretty cool.
The druid's Beast Spells feature says (5e PHB, p. 67):
Beginning at 18th level, you can cast many of your druid spells in any
shape you assume using Wild Shape. You can perform the somatic and
verbal components of a druid spell while in a beast shape, but you
aren't able to provide material components.
This is the crucial spot. It specifically says no material components. If you recall from what exactly a focus is, it is essentially a fancy material component. Meaning it can't be used, not because you can't "hold" it, but because for Game Design purposes they disallowed it.
This is further backed up by the fact that they allow somatic components (hand and body gestures) even if you don't have hands or the appropriate body part to do the somatic component, i.e. a snake making a hand sign. So holding/wearing the material component/focus is irrelevant because it is completely outlawed in RAW.
The druid's Archdruid capstone feature says (emphasis mine):
At 20th level, you can use your Wild Shape an unlimited number of
Additionally, you can ignore the verbal and somatic components of your
druid spells, as well as any material components that lack a cost
and aren't consumed by a spell. You gain this benefit in both your
natural shape and your beast shape from Wild Shape.
Doesn't this seem a bit redundant? It is because it is trying to show you that it is essentially an improvement to Beast Spells. At this point, once you reach 20th level you no longer need the material/focus component. So even at level 20 the answer is still technically no, but it becomes irrelevant because materials/focuses are no longer even needed.
However, this is D&D - so if the DM says, "Well that's stupid, you should be able to use your focus as long as you are wearing/holding it"... Then boom, there you go: the true answer is "yes, you can, so long as your DM handwaves it".
It should remain as it was, falling off or not as appropriate.
RAW, as far as I'm aware, only discuss equipment when shifting into Wild Shape, and I'm not familiar with any rules that describe anything with respect to the reverse. So from a "things do what they say they do" perspective, nothing special should happen to the beast equipment.
A creative DM might rule specific effects on a case-by-case basis: barding might stay on but be very uncomfortable when reverting forms, and might require help to remove. A saddle might just fall off. Ape-shaped boots might be way too big, or might be too tight considering the Druid's own, already-equipped boots. Horseshoes might remain partially nailed to the Druid's feet, or might fall harmlessly to the ground as the hooves disappear.
There are a lot of edge cases from other arrangements, particularly effects similar to the Druid's equipment merging into the animal form. For examples:
Some of these effects could be pretty dramatic but are not described or referenced at all in any published material, and so I would be hesitant to assume (RAI) that anything like them is possible. I would revise my opinion with a specific citation to the contrary, but my knowledge of the rules suggests that donning equipment while Wild Shaped and then reverting to normal form should have no mechanical effect of any kind.